971 plain-English guides on cross-border moves, US and Canadian returns, and small-business money. Each one ends in what to do next, and says when a written Diagnostic is the smarter first step.
Page 33 of 41, newest first.
An owner-operator's bookkeeping determines the tax bill, the audit risk, and whether they know if they're making money.
US TaxThe entity choice changes how much self-employment tax an owner-operator pays and how much liability protection exists.
US TaxIf you own or operate a truck with a taxable gross weight of 55,000 pounds or more, the IRS wants a Form 2290 from you every year.
US TaxOwner-operators pay federal excise tax on every gallon of diesel. On top of that, every state levies its own fuel tax, and the rates vary wildly.
US TaxOwner-operators are high-audit-risk taxpayers. Large deductions, cash operations, and per diem claims put truckers on the IRS radar.
US TaxHow the IRS classifies your truck lease as a true lease or conditional sale, and why the answer controls whether you deduct payments, depreciation.
US TaxThe full list of owner-operator tax deductions, how per diem works, when actual expenses beat the standard mileage rate, and what records the IRS expects.
US TaxHow taxes work for W-2 company drivers versus 1099 owner-operators, what each side can deduct, and what changes when you switch from one to the other.
US TaxSelf-employed truckers can shelter $60,000 or more per year from tax with the right retirement plan.
US TaxEach mechanism has different dollar limits, different income limitations, and different consequences when you eventually sell or trade the truck.
US TaxWhen a business withholds federal income tax, Social Security, and Medicare from employees' paychecks but does not send those withheld amounts to the IRS.
US TaxWhen you bill the federal government for costs incurred on a contract, the government does not pay for everything.
Cross-BorderUS real property is a US-situs asset for estate tax purposes, and the $60,000 NRA exemption covers almost nothing.
Cross-BorderListing a US LLC on Airbnb changes the trade-or-business classification, withholding, and FAPI on the Canadian side.
Cross-BorderA US citizen or green card holder as trustee can change a Canadian trust's US classification, trigger annual reporting.
Cross-BorderHow the US wash sale rule and Canada's superficial loss rule interact for cross-border investors harvesting tax losses across both countries.
Canadian TaxThe CRA sends different types of letters, and people call all of them "an audit." They are not the same thing.
Canadian TaxWhat happens when the CRA starts collecting: Requirements to Pay, wage garnishment, frozen accounts, liens, and the five ways to stop or slow it.
Canadian TaxWhat the CRA's gross negligence penalty under section 163(2) requires, how it differs from a regular penalty, and the burden of proof the CRA must meet.
Canadian TaxHow to file a CRA notice of objection, the 90-day deadline, what to write, real success rates, and your options if the CRA says no. Includes Form T400A.
Canadian TaxWhat to do when you disagree with a CRA reassessment. Objection deadlines, what to write, real success rates, interest during the dispute, and Tax Court.
Cross-BorderThe penalties apply even if you reported all the income from those accounts on your return and owe zero additional tax.
Cross-BorderIf you are a US person with Canadian filing obligations (or a Canadian resident with US filing obligations) and you are behind on both sides.
Cross-BorderThe wrong route can turn a zero-penalty fix into a six-figure bill, and the right route can take a potential $100,000+ exposure and resolve it for nothing.